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Orange Islands. Shit region but he was still young and relatively new to the game, but clearly had a lot of potential inside him that he had displayed at the league. Sometimes he was recognized and he felt like he was really present in the Pokemon world, a big yet familiar world that was just beginning to expand.
That's why 2k is so beloved.
Ash was the same as that during Johto but just sort of fell in to a pattern where he didn't shine anymore. I think Heroes is the last time Ash is like this.